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Debriefed

Debriefed

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During my second year of law school, I scored a summer internship at one of the biggest firms in the city.

I had high hopes the gig would lead to a future full-time job, so I was a bit of a perfectionist. I took on extra assignments all the time and even came in on weekends.

By mid-July our performance reviews were in, and when I got mine, I was absolutely gutted to see a “needs improvement” notation under the section about communication skills.

And if that slap in the face wasn’t bad enough, my boyfriend had just broken up with me.

Fired up by anger, I emailed my supervisor to ask for a meeting, and then cried in my cubicle during my lunch hour. What was wrong with me? I was smart, had high grades… and I was pretty cute-looking according to my now-ex, who repeatedly professed his weakness for my C-cup tits.

However, in the middle of my pity party, Gary — a senior partner at the firm — showed up unannounced.

“Lisa, meet me in my office at seven sharp tonight.”

Dumbfounded, I nodded as he retreated. Gary wasn’t asking. Gary never asked — he gave orders.

He was never “mean,” but I was definitely more than a little intimidated by him. According to my sources at the firm, he was in his early 50s, had no kids and was divorced from the second Mrs. Gary for years now. He kept a low profile. You never heard Gary swearing on his phone or saw him exhibiting the cocky machismo of some of the other guys at the firm.

But when Gary spoke, everyone stopped and listened.

What the hell did he want with me? Up until then, he had only acknowledged my existence with precious few words, like: “fax this please” and “thank you” when I handed him a case file.

I probably looked ridiculous to him, sitting there with a puffy, red face and tears in my eyes like a little kid. I went to the rest room, fixed my makeup and worked hard until 7 p.m.

By then, just about everyone had flown the coop. Some were out with clients or at dinner, but most had called it quits for the evening. Sure there were a few holdouts barricaded in their offices, judging by the lights coming from under a few doors. But once I got to Gary’s floor, I realized he had the place to himself. His secretary and the junior partners were all gone. His office suite was the only light at the end of the hall, and the blinds were drawn.

I took a deep breath and knocked.

“Enter.” Gary was poring over a stack of case notes at his deck. He glanced up at me nonchalantly. “Good, you’re on time.”

“I’m usually very punctual, sir.”

“That’s one of your strengths, Lisa, yes.”

Suddenly, I felt like I wanted to crawl into a hole and hide, but I just stood there, awkwardly clutching my notebook.

Gary cleared his throat. “It’s come to my attention you had some concerns about your performance review.”

“Yes, I — ”

“Your direct supervisor is out of town for the week, so he asked me to meet with you.”

“Okay.”

“Are you going to elaborate on your concerns or are you just going to stand here, wasting our time?”

“Oh — uh, sorry.” I cleared my throat. “I’ve been putting in more than 60 hours a week — as you probably know. But it says here that my communication skills are lacking. And I wanted to know why? I’ve done really well with the briefs, and client follow-ups. At least, I thought I did.”

“Yes, you have excelled at both those things.” Gary stood up and stretched.

I felt my eyes wandering; for a guy in his 50s, Gary definitely kept in shape. The salt and pepper accents to his dark hair maybe betrayed a little age, but not his face or physique, that was for sure. He was one good-looking guy.

“So then… ”

“The problem, Lisa, is your lack of confident communication in other regards. Like this meeting, for instance.”

I felt my cheeks flush. “What am I doing wrong?”

Gary sighed. “You aren’t carrying yourself correctly. If you’re going to be an asset to this firm — which I think you could be someday — then you need to become more assertive. I — we — need to see your drive and determination in person. Don’t hide behind briefs and memos. Do you understand?”

I nodded. “I guess I’m just… ”

“Shy? Well, you picked the wrong profession then.”

I hung my head, feeling the tears welling up. But that’s when I felt Gary’s touch, lifting my chin up: “You are not going to cry or fall apart when someone criticizes you, either. Is that clear?”

I bit my lip and nodded.

“Now, why don’t you use this opportunity to tell me what you really want?”

“I want a job here.”

“I know that. What else?”

Without thinking about it, I blurted out: “I don’t want to feel small anymore.”

Gary looked dead into my eyes: “Then never give anyone permission to make you feel that way.”

I must’ve appeared dumbfounded, but then I smiled and said, “Thank you for that.”

“There’s no need to thank me. Just learn to go after what you want — and never take any crap. Speaking of which, you don’t need to take on other people’s assignments, like some kind of doormat, in order to get our attention — at least, my attention.”

“His tongue swabbed my clit and probed every crease and fold.”

“Well, until now, I didn’t know you had even noticed me.”

“Of course I did.” He sat on the edge of his desk. “In fact, I’ve noticed you so much I’ve made it a point not to be your direct supervisor — otherwise, I’d be in trouble.” He was suddenly sporting a mischievous grin.

I laughed. “What are you saying?”

Gary smiled kindly and smoothed his silvery chin stubble. “I’ll let you fill in the blanks. Isn’t that what law school teaches you?

“Sometimes.”

“Well, like I said before: If there’s something you really want, you should go ahead and take it. You’ve earned it.”

I put my notebook down and started unbuttoning my blouse. “I think I’d like it better if you did the taking.”

“Is that so?”

I paused at the third button, my bra exposed. “Yes, it is.”

“Very well then.” Gary stood up and promptly ripped the rest of my blouse off, sending buttons flying. “I’ll buy you a new one.”

His fingers traced the sides of my burgundy satin bra, his eyes filled with admiration, and I suddenly felt sexier than I’d ever felt before.

“Stop wasting time and take it off,” I directed assertively.

“Hmm, now you’re learning.” Gary unhooked my bra and began sucking on my nipples. I went from giggling to moaning in 30 seconds flat.

While Gary enjoyed my breasts, he also unzipped my pencil skirt, so I was down to just my matching panties and nude thigh-highs.

“You have a boyfriend?”

“Nope, not anymore.”

“He’s a fool for missing out.” Gary slid off my panties. “Tell me what you want.”

“I’d like you to eat my pussy.”

“Then say it like you mean it — remember what we talked about.”

“Eat my pussy!”

“Good.” Gary backed me onto his desk and spread my legs wide. As his tongue swabbed my clit and probed every crease and fold, I learned why some girls never go back to dating younger guys once they’ve tried out someone older; Gary knew moves that were light years ahead of my former college-boy lovers.

In no time, he had me coming — but I wanted more. I sat up, still panting and said in my most confident voice: “I’m going to suck your dick.”

“Are you?” Gary unzipped and presented me with his erection. “You wanna swallow my cock like a hungry slut?”

I put my hands on my hips. “Yes, I do.”

“Then come here and open that pretty mouth for me, baby.”

I got down on my knees. Gary ran his hands through my hair, holding it back for me while I did my best to impress him with my blowjob skills.

“That feels good. Suck on my balls.”

I slurped his sac between my lips, while keeping a hand wrapped around his shaft. I really wanted to make him come — and to impress the living hell out of him.

But Gary made me stop before he blew his load.

“Uh-uh. Let’s not get ahead of ourselves. Turn around and put both hands on my desk.”

“I began to rub my clit while rocking my hips slowly and sensuously.”

I smiled and made a show of turning slowly and bending over, wiggling my ass enticingly. Gary gave me a few playful slaps on the butt and then plunged himself inside my soaking wet pussy. I thrashed, knocking over a stack of his papers. Gary didn’t care, though — as he would later tell me: “Sometimes you need to let the petty distractions go and focus on being in the moment.”

And that’s definitely where I was. I sure hadn’t planned to go to work that day and fuck the hot senior partner who was more than 20 years my senior. But I was really glad it was happening.

After some more deep pounding on the desk, Gary had me mount him cowgirl-style on the floor.

I moaned as I eased myself onto his thick shaft. 

“While I appreciate this gorgeous view of you, I want you to make yourself come for me.” Gary cupped my breasts and whispered, “Don’t be shy — take what you want.”

I kissed him, then sat up and began to rub my clit while rocking my hips slowly and sensuously. Of course, my attempt to take it easy didn’t last for long. The combination of being stuffed to the brim with Gary’s cock and teasing my clit soon made me frantic.

“You ready to come for me?”

“Oh yes!” I replied as I rode him wildly.

And that’s when Gary surprised me. While he was still deep inside me, he flipped us over, so I was suddenly on my back. He bent my legs, pressing my knees back to my chest. This position made every sensation even more intense as he drilled me. And then, mere seconds later, I came — and I honestly don’t know if I was seeing stars or flashing fluorescent office lights. But either way, it felt incredible.

After that orgasm, there was no turning back. We fucked until it was time for the night janitor to make his rounds. Then we went to Gary’s apartment, where we ordered in dinner and continued screwing until noon the next day.

In the end, I didn’t wind up working permanently at that firm. But after finishing law school, I opened up my own practice — with the encouragement of my much older husband.